2,3-Dimethylbenzoic acid → HCID 51306403, compound

HRID 1598438Notes

Reaction equation

HRID 1598438 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:14][C:15]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>>[CH3:14][C:15]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:18]

Participants

5

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 51306403HCID 51306403, compound

Procedure

tert-Butyl piperazine-1-carboxylate(0.50 g, 2.6 mmol), 2,3-dimethylbenzoic acid (0.44 g, 2.9 mmol), 1-hydroxybenzotriazole (HOBT) (0.45 g, 2.9 mmol) and 1-ethyl-3-(3-dimethylamino- propyl)carbodiimide hydrochloride (EDC.HCl) (0.56 g, 2.9 mmol) were added to dry, degassed dimethylformamide (7 mL). The pH of the reaction was adjusted to 7 with triethylamine, and the reaction stirred for 2 h. The dimethylformamide (DMF) was distilled in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed with 2% aqueous potassium hydrogen sulfate, saturated sodium bicarbonate solution, saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was chromatographed on silica gel using 30% ethyl acetate in hexane as eluant. The title compound was obtained as a white solid, NMR (CDCl3, 300 MHz) δ 7.17 (1H, d, J=7 Hz), 7.13 (1H, t, J=7 Hz), 6.98 (1H, d, J=7 Hz), 3.77 (2H, m), 3.51 (2H, m), 3.32 (2H, t, J=5 Hz), 3.19 (2H, m), 2.28 (3H, s), 2.18 (3H, s), 1.45 (9H, s).

Workup

  1. customto dry
  2. customdegassed dimethylformamide (7 mL)
  3. distillationThe dimethylformamide (DMF) was distilled in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 2% aqueous potassium hydrogen sulfate, saturated sodium bicarbonate solution, saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product was chromatographed on silica gel using 30% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-df473cf5c5b64f9dba136e06aabdd768
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

Loading…